US20240324450A1 - Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device - Google Patents

Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device Download PDF

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US20240324450A1
US20240324450A1 US18/558,390 US202318558390A US2024324450A1 US 20240324450 A1 US20240324450 A1 US 20240324450A1 US 202318558390 A US202318558390 A US 202318558390A US 2024324450 A1 US2024324450 A1 US 2024324450A1
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single bond
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Yusuke Takahashi
Hiroaki ITOI
Shota TANAKA
Takuto FUKAMI
Tsukasa SAWATO
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Assigned to IDEMITSU KOSAN CO.,LTD. reassignment IDEMITSU KOSAN CO.,LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FUKAMI, Takuto, ITOI, Hiroaki, SAWATO, Tsukasa, TAKAHASHI, YUSUKE, TANAKA, SHOTA
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Definitions

  • the present invention relates to a compound, a material for organic electroluminescent devices, an organic electroluminescent device, and an electronic instrument including the organic electroluminescent device.
  • an organic electroluminescent device (hereinafter sometimes referred to as “organic EL device”) is composed of an anode, a cathode, and an organic layer interposed between the anode and the cathode.
  • organic EL device In application of a voltage between the two electrodes, electrons from the cathode side and holes from the anode side are injected into a light emitting region, and the injected electrons and holes are recombined in the light emitting region to generate an excited state, which then returns to the ground state to emit light.
  • PTLs 1 to 4 disclose compounds for use as a material for organic electroluminescent devices.
  • the present invention provides a material for organic EL devices, the material containing the compound represented by the formula (1).
  • the present invention provides an organic electroluminescent device including a cathode, an anode, and an organic layer disposed between the cathode and the anode, the organic layer including a light emitting layer, at least one layer of the organic layer containing the compound represented by the formula (1).
  • the present invention provides an electronic instrument including the organic electroluminescent device.
  • the organic EL device containing the compound represented by the formula (1) shows an improved device performance.
  • FIG. 1 is a schematic diagram illustrating an example of the layer configuration of the organic EL device according to an aspect of the present invention.
  • FIG. 2 is a schematic diagram illustrating another example of the layer configuration of the organic EL device according to an aspect of the present invention.
  • FIG. 3 is a schematic diagram illustrating still another example of the layer configuration of the organic EL device according to an aspect of the present invention.
  • the hydrogen atom encompasses isotopes thereof having different numbers of neutrons, i.e., protium, deuterium, and tritium.
  • the bonding site where the symbol, such as “R”, or “D” representing a deuterium atom is not shown is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded thereto.
  • the number of ring carbon atoms shows the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure including atoms bonded to form a ring (such as a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
  • a ring such as a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound.
  • the carbon atom contained in the substituent is not included in the number of ring carbon atoms.
  • the same definition is applied to the “number of ring carbon atoms” described hereinafter unless otherwise indicated.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • 9,9-diphenylfluorenyl group has 13 ring carbon atoms
  • 9,9′-spirobifluorenyl group has 25 ring carbon atoms.
  • a benzene ring having, for example, an alkyl group substituted thereon as a substituent the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Accordingly, a benzene ring having an alkyl group substituted thereon has 6 ring carbon atoms.
  • a naphthalene ring having, for example, an alkyl group substituted thereon as a substituent the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Accordingly, a naphthalene ring having an alkyl group substituted thereon has 10 ring carbon atoms.
  • the number of ring atoms shows the number of atoms constituting the ring itself of a compound having a structure including atoms bonded to form a ring (such as a monocyclic ring, a condensed ring, and a set of rings) (such as a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
  • a ring such as a monocyclic ring, a condensed ring, and a set of rings
  • the atom that does not constitute the ring such as a hydrogen atom terminating the bond of the atom constituting the ring
  • the atom contained in the substituent are not included in the number of ring atoms.
  • a pyridine ring has 6 ring atoms
  • a quinazoline ring has 10 ring atoms
  • a furan ring has 5 ring atoms.
  • the number of hydrogen atoms bonded to a pyridine ring or atoms constituting a substituent is not included in the number of ring atoms of the pyridine ring. Accordingly, a pyridine ring having a hydrogen atom or a substituent bonded thereto has 6 ring atoms.
  • a quinazoline ring having a hydrogen atom or a substituent bonded thereto has 10 ring atoms.
  • the expression “having XX to YY carbon atoms” in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” means the number of carbon atoms of the unsubstituted ZZ group, and, in the case where the ZZ group is substituted, the number of carbon atoms of the substituent is not included.
  • YY is larger than “XX”, “XX” represents an integer of 1 or more, and “YY” represents an integer of 2 or more.
  • the expression “having XX to YY atoms” in the expression “substituted or unsubstituted ZZ group having XX to YY atoms” means the number of atoms of the unsubstituted ZZ group, and, in the case where the ZZ group is substituted, the number of atoms of the substituent is not included.
  • YY is larger than “XX”, “XX” represents an integer of 1 or more, and “YY” represents an integer of 2 or more.
  • an unsubstituted ZZ group means the case where the “substituted or unsubstituted ZZ group” is an “unsubstituted ZZ group”
  • a substituted ZZ group means the case where the “substituted or unsubstituted ZZ group” is a “substituted ZZ group”.
  • the expression “unsubstituted” in the expression “substituted or unsubstituted ZZ group” means that hydrogen atoms in the ZZ group are not substituted by a substituent.
  • the hydrogen atoms in the “unsubstituted ZZ group” each are a protium atom, a deuterium atom, or a tritium atom.
  • the expression “substituted” in the expression “substituted or unsubstituted ZZ group” means that one or more hydrogen atom in the ZZ group is substituted by a substituent.
  • the expression “substituted” in the expression “BB group substituted by an AA group” similarly means that one or more hydrogen atom in the BB group is substituted by the AA group.
  • the number of ring carbon atoms of the “unsubstituted aryl group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.
  • the number of ring atoms of the “unsubstituted heterocyclic group” is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise indicated in the description.
  • the number of carbon atoms of the “unsubstituted alkyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise indicated in the description.
  • the number of carbon atoms of the “unsubstituted alkenyl group” is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise indicated in the description.
  • the number of carbon atoms of the “unsubstituted alkynyl group” is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise indicated in the description.
  • the number of ring carbon atoms of the “unsubstituted cycloalkyl group” is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise indicated in the description.
  • the number of ring carbon atoms of the “unsubstituted arylene group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.
  • the number of ring atoms of the “unsubstituted divalent heterocyclic group” is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise indicated in the description.
  • the number of carbon atoms of the “unsubstituted alkylene group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise indicated in the description.
  • specific examples (set of specific examples G1) of the “substituted or unsubstituted aryl group” include the unsubstituted aryl groups (set of specific examples G1A) and the substituted aryl groups (set of specific examples G1B) shown below.
  • the unsubstituted aryl group means the case where the “substituted or unsubstituted aryl group” is an “unsubstituted aryl group”, and the substituted aryl group means the case where the “substituted or unsubstituted aryl group” is a “substituted aryl group”.
  • the simple expression “aryl group” encompasses both the “unsubstituted aryl group” and the “substituted aryl group”.
  • the “substituted aryl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted aryl group” by a substituent.
  • Examples of the “substituted aryl group” include groups formed by one or more hydrogen atom of each of the “unsubstituted aryl groups” in the set of specific examples G1A by a substituent, and the examples of the substituted aryl groups in the set of specific examples G1B.
  • the examples of the “unsubstituted aryl group” and the examples of the “substituted aryl group” enumerated herein are mere examples, and the “substituted aryl group” in the description herein encompasses groups formed by substituting a hydrogen atom bonded to the carbon atom of the aryl group itself of each of the “substituted aryl groups” in the set of specific examples G1B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted aryl groups” in the set of specific examples G1B by a substituent.
  • heterocyclic group means a cyclic group containing at least one hetero atom in the ring atoms.
  • the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
  • heterocyclic group is a monocyclic group or a condensed ring group.
  • heterocyclic group is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • specific examples (set of specific examples G2) of the “substituted or unsubstituted heterocyclic group” include the unsubstituted heterocyclic groups (set of specific examples G2A) and the substituted heterocyclic groups (set of specific examples G2B) shown below.
  • the unsubstituted heterocyclic group means the case where the “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”
  • the substituted heterocyclic group means the case where the “substituted or unsubstituted heterocyclic group” is a “substituted heterocyclic group”.
  • the simple expression “heterocyclic group” encompasses both the “unsubstituted heterocyclic group” and the “substituted heterocyclic group”.
  • the “substituted heterocyclic group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted heterocyclic group” by a substituent.
  • Specific examples of the “substituted heterocyclic group” include groups formed by substituting a hydrogen atom of each of the “unsubstituted heterocyclic groups” in the set of specific examples G2A by a substituent, and the examples of the substituted heterocyclic groups in the set of specific examples G2B.
  • the examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” enumerated herein are mere examples, and the “substituted heterocyclic group” in the description herein encompasses groups formed by substituting a hydrogen atom bonded to the ring atom of the heterocyclic group itself of each of the “substituted heterocyclic groups” in the set of specific examples G2B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted heterocyclic groups” in the set of specific examples G2B by a substituent.
  • the set of specific examples G2A includes, for example, the unsubstituted heterocyclic group containing a nitrogen atom (set of specific examples G2A1), the unsubstituted heterocyclic group containing an oxygen atom (set of specific examples G2A2), the unsubstituted heterocyclic group containing a sulfur atom (set of specific examples G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from each of the ring structures represented by the following general formulae (TEWP-16) to (TEWP-33) (set of specific examples G2A4).
  • the set of specific examples G2B includes, for example, the substituted heterocyclic groups containing a nitrogen atom (set of specific examples G2B1), the substituted heterocyclic groups containing an oxygen atom (set of specific examples G2B2), the substituted heterocyclic groups containing a sulfur atom (set of specific examples G2B3), and groups formed by substituting one or more hydrogen atom of each of monovalent heterocyclic groups derived from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) by a substituent (set of specific examples G2B4).
  • the substituted heterocyclic groups containing a nitrogen atom set of specific examples G2B1
  • the substituted heterocyclic groups containing an oxygen atom set of specific examples G2B2
  • the substituted heterocyclic groups containing a sulfur atom set of specific examples G2B3
  • X A and Y A each independently represent an oxygen atom, a sulfur atom, NH, or CH 2 , provided that at least one of X A and Y A represents an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic groups derived from the ring structures represented by the general formulae (TEMP-16) to (TEMP-33) include monovalent groups formed by removing one hydrogen atom from the NH or CH 2 .
  • the unsubstituted alkyl group means the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”
  • the substituted alkyl group means the case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group”.
  • the simple expression “alkyl group” encompasses both the “unsubstituted alkyl group” and the “substituted alkyl group”.
  • the “unsubstituted alkyl group” encompasses an “unsubstituted linear alkyl group” and an “unsubstituted branched alkyl group”.
  • the examples of the “unsubstituted alkyl group” and the examples of the “substituted alkyl group” enumerated herein are mere examples, and the “substituted alkyl group” in the description herein encompasses groups formed by substituting a hydrogen atom of the alkyl group itself of each of the “substituted alkyl groups” in the set of specific examples G3B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted alkyl groups” in the set of specific examples G3B by a substituent.
  • the unsubstituted alkenyl group means the case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group”
  • the substituted alkenyl group means the case where the “substituted or unsubstituted alkenyl group” is a “substituted alkenyl group”.
  • the simple expression “alkenyl group” encompasses both the “unsubstituted alkenyl group” and the “substituted alkenyl group”.
  • the “substituted alkenyl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted alkenyl group” by a substituent.
  • Specific examples of the “substituted alkenyl group” include the “unsubstituted alkenyl groups” (set of specific examples G4A) that each have a substituent, and the examples of the substituted alkenyl groups (set of specific examples G4B).
  • the examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” enumerated herein are mere examples, and the “substituted alkenyl group” in the description herein encompasses groups formed by substituting a hydrogen atom of the alkenyl group itself of each of the “substituted alkenyl groups” in the set of specific examples G4B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of each of the “substituted alkenyl groups” in the set of specific examples G4B by a substituent.
  • specific examples (set of specific examples G5) of the “substituted or unsubstituted alkynyl group” include the unsubstituted alkynyl group (set of specific examples G5A) shown below.
  • the unsubstituted alkynyl group means the case where the “substituted or unsubstituted alkynyl group” is an “unsubstituted alkynyl group”.
  • the simple expression “alkynyl group” encompasses both the “unsubstituted alkynyl group” and the “substituted alkynyl group”.
  • the “substituted alkynyl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted alkynyl group” by a substituent.
  • Specific examples of the “substituted alkenyl group” include groups formed by substituting one or more hydrogen atom of the “unsubstituted alkynyl group” (set of specific examples G5A) by a substituent.
  • specific examples (set of specific examples G6) of the “substituted or unsubstituted cycloalkyl group” include the unsubstituted cycloalkyl groups (set of specific examples G6A) and the substituted cycloalkyl group (set of specific examples G6B) shown below.
  • the unsubstituted cycloalkyl group means the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and the substituted cycloalkyl group means the case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group”.
  • the simple expression “cycloalkyl group” encompasses both the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group”.
  • the “substituted cycloalkyl group” means a group formed by substituting one or more hydrogen atom of the “unsubstituted cycloalkyl group” by a substituent.
  • Specific examples of the “substituted cycloalkyl group” include groups formed by substituting one or more hydrogen atom of each of the “unsubstituted cycloalkyl groups” (set of specific examples G6A) by a substituent, and the example of the substituted cycloalkyl group (set of specific examples G6B).
  • the examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” enumerated herein are mere examples, and the “substituted cycloalkyl group” in the description herein encompasses groups formed by substituting one or more hydrogen atom bonded to the carbon atoms of the cycloalkyl group itself of the “substituted cycloalkyl group” in the set of specific examples G6B by a substituent, and groups formed by substituting a hydrogen atom of the substituent of the “substituted cycloalkyl group” in the set of specific examples G6B by a substituent.
  • G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,
  • G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,
  • G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and
  • G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.
  • G1 in —Si(G1)(G1)(G1) are the same as or different from each other.
  • G2 in —Si(G1)(G2)(G2) are the same as or different from each other.
  • G1 in —Si(G1)(G1)(G2) are the same as or different from each other.
  • G2 in —Si(G2)(G2)(G2) are the same as or different from each other.
  • G3 Plural groups represented by G3 in —Si(G3)(G3)(G3) are the same as or different from each other.
  • G6 in —Si(G6)(G6)(G6) are the same as or different from each other.
  • G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,
  • G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,
  • G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and
  • G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.
  • G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,
  • G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,
  • G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and
  • G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.
  • G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1,
  • G2 represents the “substituted or unsubstituted heterocyclic group” described in the set of specific examples G2,
  • G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and
  • G6 represents the “substituted or unsubstituted cycloalkyl group” described in the set of specific examples G6.
  • G1 in —N(G1)(G1) are the same as or different from each other.
  • G2 in —N(G2)(G2) are the same as or different from each other.
  • G3 in —N(G3)(G3) are the same as or different from each other.
  • G6 in —N(G6)(G6) are the same as or different from each other.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the “substituted or unsubstituted fluoroalkyl group” means a group formed by substituting at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” by a fluorine atom, and encompasses a group formed by substituting all the hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” by fluorine atoms (i.e., a perfluoroalkyl group).
  • the number of carbon atoms of the “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description.
  • the “substituted fluoroalkyl group” means a group formed by substituting one or more hydrogen atom of the “fluoroalkyl group” by a substituent.
  • the “substituted fluoroalkyl group” encompasses a group formed by substituting one or more hydrogen atom bonded to the carbon atom of the alkyl chain in the “substituted fluoroalkyl group” by a substituent, and a group formed by substituting one or more hydrogen atom of the substituent in the “substituted fluoroalkyl group” by a substituent.
  • Specific examples of the “unsubstituted fluoroalkyl group” include examples of groups formed by substituting one or more hydrogen atom in each of the “alkyl group” (set of specific examples G3) by a fluorine atom.
  • the “substituted or unsubstituted haloalkyl group” means a group formed by substituting at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” by a halogen atom, and encompasses a group formed by substituting all the hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” by halogen atoms.
  • the number of carbon atoms of the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description.
  • the “substituted haloalkyl group” means a group formed by substituting one or more hydrogen atom of the “haloalkyl group” by a substituent.
  • the “substituted haloalkyl group” encompasses a group formed by substituting one or more hydrogen atom bonded to the carbon atom of the alkyl chain in the “substituted haloalkyl group” by a substituent, and a group formed by substituting one or more hydrogen atom of the substituent in the “substituted haloalkyl group” by a substituent.
  • Specific examples of the “unsubstituted haloalkyl group” include examples of groups formed by substituting one or more hydrogen atom in each of the “alkyl group” (set of specific examples G3) by a halogen atom.
  • a haloalkyl group may be referred to as a halogenated alkyl group in some cases.
  • specific examples of the “substituted or unsubstituted alkoxy group” include a group represented by —O(G3), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3.
  • the number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description.
  • specific examples of the “substituted or unsubstituted alkylthio group” include a group represented by —S(G3), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3.
  • the number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise indicated in the description.
  • specific examples of the “substituted or unsubstituted aryloxy group” include a group represented by —O(G1), wherein G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1.
  • the number of ring carbon atoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.
  • specific examples of the “substituted or unsubstituted arylthio group” include a group represented by —S(G1), wherein G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1.
  • the number of ring carbon atoms of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise indicated in the description.
  • trialkylsilyl group examples include a group represented by —Si(G3)(G3)(G3), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3.
  • Plural groups represented by G3 in —Si(G3)(G3)(G3) are the same as or different from each other.
  • the number of carbon atoms of each of alkyl groups of the “substituted or unsubstituted trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise indicated in the description.
  • specific examples of the “substituted or unsubstituted aralkyl group” include a group represented by -(G3)-(G1), wherein G3 represents the “substituted or unsubstituted alkyl group” described in the set of specific examples G3, and G1 represents the “substituted or unsubstituted aryl group” described in the set of specific examples G1.
  • the “aralkyl group” is a group formed by substituting a hydrogen atom of an “alkyl group” by an “aryl group” as a substituent, and is one embodiment of the “substituted alkyl group”.
  • the “unsubstituted aralkyl group” is an “unsubstituted alkyl group” that is substituted by an “unsubstituted aryl group”, and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise indicated in the description.
  • substituted or unsubstituted aralkyl group examples include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an ⁇ -naphthylmethyl group, a 1- ⁇ -naphthylethyl group, a 2- ⁇ -naphthylethyl group, a 1- ⁇ -naphthylisopropyl group, a 2- ⁇ -naphthylisopropyl group, a Q-naphthylmethyl group, a 1- ⁇ -naphthylethyl group, a 2-O-naphthylethyl group, a 1- ⁇ -naphthylisopropyl group, and a 2- ⁇ -n
  • the substituted or unsubstituted aryl group is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl
  • the substituted or unsubstituted heterocyclic group is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (e.g., a 1-carbazolyl, group, a 2-carbazolyl, group, a 3-carbazolyl, group, a 4-carbazolyl, group, or a 9-carbazolyl, group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranly group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a diazadibenzo
  • the carbazolyl group is specifically any one of the following groups unless otherwise indicated in the description.
  • the (9-phenyl)carbazolyl group is specifically any one of the following groups unless otherwise indicated in the description.
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following groups unless otherwise indicated in the description.
  • the substituted or unsubstituted alkyl group is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a t-butyl group, or the like unless otherwise indicated in the description.
  • the “substituted or unsubstituted arylene group” is a divalent group derived by removing one hydrogen atom on the aryl ring from the “substituted or unsubstituted aryl group” described above unless otherwise indicated in the description.
  • Specific examples (set of specific examples G12) of the “substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the “substituted or unsubstituted aryl groups” described in the set of specific examples G1.
  • the “substituted or unsubstituted divalent heterocyclic group” is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the “substituted or unsubstituted heterocyclic group” described above unless otherwise indicated in the description.
  • Specific examples (set of specific examples G13) of the “substituted or unsubstituted divalent heterocyclic group” include divalent groups derived by removing one hydrogen atom on the heterocyclic ring from the “substituted or unsubstituted heterocyclic groups” described in the set of specific examples G2.
  • the “substituted or unsubstituted alkylene group” is a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” described above unless otherwise indicated in the description.
  • Specific examples (set of specific examples G14) of the “substituted or unsubstituted alkylene group” include divalent groups derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl groups” described in the set of specific examples G3.
  • the substituted or unsubstituted arylene group is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68) unless otherwise indicated in the description.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • the formulae Q 9 and Q 10 may be bonded to each other to form a ring via a single bond.
  • * represents a bonding site.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • the substituted or unsubstituted divalent heterocyclic group is preferably the groups represented by the following general formulae (TEMP-69) to (TEMP-102) unless otherwise indicated in the description.
  • Q 1 to Q 9 each independently represent a hydrogen atom or a substituent.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • the case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted monocyclic ring, or each are bonded to each other to form a substituted or unsubstituted condensed ring, or each are not bonded to each other” means a case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted monocyclic ring”, a case where “one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted condensed ring”, and a case where “one or more combinations of combinations each including adjacent two or more each are not bonded to each other”.
  • the combinations each including adjacent two as one combination include a combination of R 921 and R 922 , a combination of R 922 and R 923 , a combination of R 923 and R 924 , a combination of R 924 and R 930 , a combination of R 930 and R 925 , a combination of R 925 and R 926 , a combination of R 926 and R 927 , a combination of R 927 and R 928 , a combination of R 928 and R 929 , and a combination of R 929 and R 921 .
  • the “one or more combinations” mean that two or more combinations each including adjacent two or more may form rings simultaneously.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
  • the “combination including adjacent two or more forms rings” encompasses not only the case where adjacent two included in the combination are bonded as in the aforementioned example, but also the case where adjacent three or more included in the combination are bonded.
  • this case means that R 921 and R 922 are bonded to each other to form a ring Q A , R 922 and R 923 are bonded to each other to form a ring Q C , and adjacent three (R 921 , R 922 , and R 923 ) included in the combination are bonded to each other to form rings, which are condensed to the anthracene core skeleton, and in this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), the ring Q A and the ring Q C share R 922 .
  • the formed “monocyclic ring” or “condensed ring” may be a saturated ring or an unsaturated ring in terms of structure of the formed ring itself.
  • the “monocyclic ring” or the “condensed ring” may form a saturated ring or an unsaturated ring.
  • the ring Q A and the ring Q B formed in the general formula (TEMP-104) each are a “monocyclic ring” or a “condensed ring”.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) each are a “condensed ring”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) form a condensed ring through condensation of the ring Q A and the ring Q C .
  • the ring Q A in the general formula (TMEP-104) is a benzene ring
  • the ring Q A is a monocyclic ring.
  • the ring Q A in the general formula (TMEP-104) is a naphthalene ring
  • the ring Q A is a condensed ring.
  • the “unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • the “saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • aromatic hydrocarbon ring examples include the structures formed by terminating the groups exemplified as the specific examples in the set of specific examples G1 with a hydrogen atom.
  • aromatic heterocyclic ring examples include the structures formed by terminating the aromatic heterocyclic groups exemplified as the specific examples in the set of specific examples G2 with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include the structures formed by terminating the groups exemplified as the specific examples in the set of specific examples G6 with a hydrogen atom.
  • the expression “to form a ring” means that the ring is formed only with the plural atoms of the core structure or with the plural atoms of the core structure and one or more arbitrary element.
  • the ring Q A formed by bonding R 921 and R 922 each other shown in the general formula (TEMP-104) means a ring formed with the carbon atom of the anthracene skeleton bonded to R 921 , the carbon atom of the anthracene skeleton bonded to R 922 , and one or more arbitrary element.
  • the ring Q A is formed with R 921 and R 922
  • a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton bonded to R 921
  • the carbon atom of the anthracene skeleton bonded to R 922 is a benzene ring.
  • the number of the “one or more arbitrary element” constituting the monocyclic ring or the condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less, unless otherwise indicated in the description.
  • the “monocyclic ring” is preferably a benzene ring unless otherwise indicated in the description.
  • the “unsaturated ring” is preferably a benzene ring unless otherwise indicated in the description.
  • the “one or more combinations of combinations each including adjacent two or more” each are “bonded to each other to form a substituted or unsubstituted monocyclic ring”, or each are “bonded to each other to form a substituted or unsubstituted condensed ring”, it is preferred that the one or more combinations of combinations each including adjacent two or more each are bonded to each other to form a substituted or unsubstituted “unsaturated ring” containing the plural atoms of the core skeleton and 1 or more and 15 or less at least one kind of an element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise indicated in the description.
  • the substituent is, for example, an “arbitrary substituent” described later.
  • specific examples of the substituent include the substituents explained in the section “Substituents in Description” described above.
  • the substituent is, for example, an “arbitrary substituent” described later.
  • specific examples of the substituent include the substituents explained in the section “Substituents in Description” described above.
  • substituent for “Substituted or Unsubstituted” is, for example, a group selected from the group consisting of
  • the substituent for the case of “substituted or unsubstituted” may be a group selected from the group consisting of
  • the substituent for the case of “substituted or unsubstituted” may be a group selected from the group consisting of
  • the arbitrary adjacent substituents may form a “saturated ring” or an “unsaturated ring”, preferably form a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably form a benzene ring, unless otherwise indicated.
  • the arbitrary substituent may further have a substituent unless otherwise indicated in the description.
  • the definition of the substituent that the arbitrary substituent further has may be the same as the arbitrary substituent.
  • a numerical range shown by “AA to BB” means a range including the numerical value AA as the former of “AA to BB” as the lower limit value and the numerical value BB as the latter of “AA to BB” as the upper limit value.
  • the compound of the present invention is represented by the formula (1).
  • signs in the formula (1) and each formula, which will be described later, included in the formula (1) will be described. Unless otherwise specified, the same signs have the same meaning.
  • Adjacent two selected from R 1 to R 4 are not bonded to each other, thus forming no ring.
  • the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 1 to R 4 is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group, preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, and more preferably a methyl group or a t-butyl group.
  • the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R 1 to R 4 is, for example, a phenyl group, a biphenylyl group, a biphenylenyl group, or a naphthyl group, preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group, and more preferably a phenyl group.
  • All of R 1 to R 4 may be a hydrogen atom.
  • L 1 to L 4 are each independently a single bond, an unsubstituted arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 12 ring carbon atoms, or an unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 13 ring atoms.
  • L 1 to L 4 are each independently preferably a single bond, or an unsubstituted arylene group having 6 to 30 ring carbon atoms.
  • L 3 is preferably a single bond.
  • L 4 is preferably a single bond.
  • the unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L 1 to L 4 refers to a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the unsubstituted aryl group having 6 to 30 ring carbon atoms is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzocrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group, preferably a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group, more preferably a pheny
  • the unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by L 1 to L 4 refers to a divalent group obtained by removing one hydrogen atom from an unsubstituted heterocyclic group.
  • the unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms represented by L 1 to L 4 is, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 12 ring carbon atoms constituted only of 6-membered rings, a substituted or unsubstituted heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 13 ring atoms, or a group represented by the following formula (a).
  • * 1 is a bonding site to L 1 or L 2 .
  • R a and R b are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 13 ring atoms.
  • R a and R b may be bonded to each other to form a substituted or unsubstituted ring, or may not be bonded to each other, thus forming no ring.
  • R a and R b are each independently preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R a and R b is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group, preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group, more preferably a methyl group,
  • the unsubstituted monocyclic ring formed by R a and R b is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring.
  • the unsubstituted condensed ring formed by R a and R b is, for example, a naphthalene ring or an anthracene ring.
  • R a and R b when R a and R b are bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted condensed ring, R a and R b may form a ring with a fluorene skeleton to which they are bonded to form a spiro ring.
  • the spiro ring is a hydrocarbon ring or a heterocyclic ring, and is selected from a monocyclic ring, a condensed ring, a bridged bicyclo ring, and a bridged tricyclo ring.
  • * indicates a bonding site of the fluorene skeleton to the benzene ring.
  • R 21 to R 28 is a single bond bonded to *2, and R 21 to R 28 that are not a single bond bonded to *2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, adjacent two selected from R 21 to R 28 that are not the single bond may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other, thus forming no ring.
  • R 22 to R 27 is a single bond bonded to *2
  • Ar 1 and Ar 2 are groups represented by the formula (a)
  • R 22 or R 27 is a single bond bonded to *2
  • at least one selected from two R a 's and two R's is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • All of R 21 to R 28 that are not a single bond bonded to *2 may be a hydrogen atom.
  • Ar 1 and Ar 2 are each independently preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms constituted only of 6-membered rings, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms constituted only of 6-membered rings.
  • Ar 1 and Ar 2 are each independently preferably a group represented by any of the following formulas (1a) to (1e), and more preferably a group represented by any of the following formulas (1a), (1b) and (1d).
  • Adjacent two selected from R 101 to R 105 that are not the single bond are not bonded to each other, thus forming no ring, adjacent two selected from R 106 to R 110 that are not the single bond are not bonded to each other, thus forming no ring.
  • All of R 101 to R 110 that are not a single bond bonded to *22 or a single bond bonded to *23 may be a hydrogen atom.
  • k is 0 and 1 is 0.
  • *23 represents *21
  • the formula (Ia) is represented by the following formula.
  • k is 1 and 1 is 0.
  • *23 represents *22
  • the formula (Ia) is represented by the following formula.
  • k is 0 and 1 is 1.
  • *22 represents *21
  • the formula (Ia) is represented by the following formula.
  • k is 1 and 1 is 1.
  • the formula (Ia) is represented by the following formula.
  • k+1 is preferably 1.
  • R 111 to R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • Adjacent two selected from R 111 to R 115 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other, thus forming no ring.
  • All of R 111 to R 115 may be a hydrogen atom.
  • a group represented by the formula (Ia) is preferably represented by the following formula.
  • R is omitted for simplification.
  • the formula (Ib) is represented by the following formula.
  • R 121 is preferably a single bond bonded to *25, and in another aspect, R 122 is preferably a single bond bonded to *25.
  • All of R 121 to R 128 that are not a single bond bonded to *25 may be a hydrogen atom.
  • R 131 to R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,
  • R 131 , R 132 , and R 140 is preferably a single bond bonded to *27.
  • R 131 is a single bond bonded to *27
  • R 132 is a single bond bonded to *27
  • R 140 is a single bond bonded to *27. All of R 131 to R 140 that are not a single bond bonded to *27 may be a hydrogen atom.
  • the formula (1d) is represented by the following formula.
  • X 2 is an oxygen atom, a sulfur atom, or NR A .
  • X 2 is preferably an oxygen atom or NR A .
  • R A is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • R 141 to R 148 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, provided that one selected from R 141 to R 148 and R A is a single bond bonded to *29.
  • At least one adjacent two selected from R 141 to R 148 that are not the single bond may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other, thus forming no ring.
  • All of R 141 to R 148 and R A that are not a single bond bonded to *29 may be a hydrogen atom.
  • R 141 to R 144 is a single bond bonded to *29.
  • R A is a single bond bonded to *29, an unsubstituted phenyl group, or a naphthyl group.
  • the formula (1e) is represented by the following formula.
  • R 151 to R 15 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group,
  • Adjacent two selected from R 151 to R 155 that are neither a single bond bonded to *31 nor a single bond bonded to *32 are not bonded to each other, thus forming no ring.
  • All of R 151 to R 155 that are neither a single bond bonded to *31 nor a single bond bonded to *32 may be a hydrogen atom.
  • R 161 to R 165 and R 171 to R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms,
  • At least one adjacent two selected from R 171 to R 175 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other, thus forming no ring.
  • R 161 to R 165 and R 171 to R 175 Details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R 161 to R 165 and R 171 to R 175 are as described for R 1 to R 4 . All of R 161 to R 165 and R 171 to R 175 may be a hydrogen atom.
  • the formula (1e) includes groups represented by the following formulas (1e-1) to (1e-5), with the formulas (1e-1), (1e-2) or (1e-4) being preferred.
  • Ar 3 is a group represented by the following formula (x).
  • halogen atom represented by R 31 to R 38 , R 41 to R 44 , and R 51 to R 58 are as described in the section “Substituents in Description”, and preferred is a fluorine atom.
  • the unsubstituted alkyl group represented by R 31 to R 38 , R 41 to R 44 , and R 51 to R 58 is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and still more preferably a methyl group or a t-butyl group.
  • the unsubstituted cycloalkyl group represented by R 31 to R 38 , R 41 to R 44 , and R 51 to R 58 is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, or a 2-norbornyl group, and more preferably a cyclopentyl group or a cyclohexyl group.
  • the unsubstituted aryl group represented by R 1 to R 8 and R 11 to R 18 is preferably a phenyl group, a biphenyl group, or a phenanthryl group, more preferably a phenyl group, a biphenyl group, or a naphthyl group, and further preferably a phenyl group.
  • n 0 or 1.
  • R 31 and R 32 , R 32 and R 33 , or R 33 and R 34 is a single bond bonded to *a, and the other is a single bond bonded to *b,
  • R 31 and R 32 , R 32 and R 33 , or R 33 and R 34 is a single bond bonded to *a, and the other is a single bond bonded to *b,
  • R 31 and R 32 , R 32 and R 33 , or R 33 and R 34 is a single bond bonded to *a, and the other is a single bond bonded to *b,
  • R 31 and R 32 , R 32 and R 33 , or R 33 and R 34 is a single bond bonded to *a, and the other is a single bond bonded to *b,
  • n 0.
  • n 0.
  • n is 0.
  • R 31 to R 33 that are not a single bond bonded to *a and *b
  • R 36 to R 38 is a single bond bonded to *4
  • R 31 and R 32 that are not a single bond bonded to *a and *b
  • R 37 and R 38 is a single bond bonded to *4
  • R 32 or R 37 that is not a single bond bonded to *a and *b is a single bond bonded to *4.
  • X 1 is an oxygen atom or a sulfur atom.
  • X 1 is preferably an oxygen atom.
  • a “hydrogen atom” as used herein includes a light hydrogen atom, a deuterium atom, and a tritium atom.
  • the inventive compound may contain a naturally-derived deuterium atom.
  • a deuterium atom may also be intentionally introduced in the compound (1) by using a deuterated compound in a part or all of raw material compounds.
  • the compound (1) contains at least one deuterium atom.
  • the inventive compound may be a compound represented by the formula (1), at least one of the hydrogen atoms contained in the compound being a deuterium atom.
  • At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom (in the following, “substituted or unsubstituted”, the number of carbon atoms, and the number of atoms are omitted):
  • the deuteration ratio of the inventive compound depends on the deuteration ratio of the raw material compound used. Even when a raw material having a predetermined deuteration ratio is used, light hydrogen isomers may be contained at a certain naturally-derived ratio. Thus, the aspects of the deuteration ratio of the inventive compound shown below are a ratio obtained by taking a minor amount of naturally-derived isomers into account based on a ratio obtained by simply counting the number of deuterium atoms shown by the chemical formula.
  • the deuteration ratio of the inventive compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, furthermore preferably 10% or more, and still furthermore preferably 50% or more.
  • the inventive compound may be a mixture containing a deuterated compound and a non-deuterated compound or a mixture of two or more compounds having different deuteration ratios.
  • the deuteration ratio of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, furthermore preferably 10% or more, still furthermore preferably 50% or more, and less than 100%.
  • the ratio of the number of the deuterium atoms based on the number of all the hydrogen atoms in the inventive compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, furthermore preferably 10% or more, and 100% or less.
  • a “substituted or unsubstituted XX group” included in the definitions of the above formulas is a substituted XX group
  • substituents for ‘Substituted or Unsubstituted’ are as described in “Substituents for ‘Substituted or Unsubstituted’”, and is preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, or an aromatic heterocyclic group having 5 to 13 ring atoms, and more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring carbon atoms. Details of each group are as described above.
  • the inventive compound can be easily produced by a person skilled in the art with reference to synthetic examples described below and known synthetic methods.
  • inventive compound will be shown below, but were not limited to the exemplified compounds.
  • D represents a deuterium atom
  • the material for organic EL devices of the present invention contains the inventive compound.
  • the content of the inventive compound in the material for organic EL devices is 1% by mass or more (including 100%), preferably coo by mass or more (including 100), more preferably 50% by mass or more (including 1000%), further preferably 80% by mass or more (including 1000%), and particularly preferably 90% by mass or more (including 1000%).
  • the material for organic EL devices of the present invention is useful for production of an organic EL device.
  • the organic EL device of the present invention includes an anode, a cathode, and organic layers disposed between the anode and the cathode.
  • the organic layers include a light emitting layer and at least one of the organic layers contains the inventive compound.
  • organic layer containing the inventive compound examples include, but not limited to, a hole transporting zone (hole injecting layer, hole transporting layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light emitting layer, the light emitting layer, a space layer, and an electron transporting zone (electron injecting layer, electron transporting layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer.
  • a hole transporting zone hole injecting layer, hole transporting layer, electron blocking layer, exciton blocking layer, etc.
  • an electron transporting zone electron injecting layer, electron transporting layer, hole blocking layer, etc.
  • the inventive compound is preferably used as a material for the hole transporting zone or light emitting layer, more preferably as a material for the hole transporting zone, further preferably as a material for the hole injecting layer, hole transporting layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injecting layer or hole transporting layer, of a fluorescent or phosphorescent EL device.
  • the organic EL device of the present invention may be a fluorescence or phosphorescence emission type monochromatic luminescent device, a fluorescence/phosphorescence hybrid type white luminescent device, a simple type having a single light emitting unit, or a tandem type having two or more light emitting units, and is preferably a fluorescence emission type device.
  • the “light emitting unit” refers to a minimum unit that includes organic layers, at least one of which is a light emitting layer, and that emits light by recombination of injected holes and injected electrons.
  • An example of a typical device configuration of the simple type organic EL device is the following device configuration.
  • the light emitting unit may be a multilayer type having two or more phosphorescence emitting layers and fluorescence emitting layers, and in this case, a space layer may be provided between the light emitting layers for the purpose of preventing excitons generated in the phosphorescence emitting layers from diffusing into the fluorescence emitting layers.
  • a typical layer configuration of the simple type light emitting unit is shown below. The layers in parentheses are optional.
  • the phosphorescence or fluorescence emitting layers described above can exhibit luminescent colors different from one another.
  • a specific example of the layer configuration is a layer configuration in the light emitting unit (f) of (hole injecting layer/) hole transporting layer/first phosphorescence emitting layer (red light emission)/second phosphorescence emitting layer (green light emission)/space layer/fluorescence emitting layer (blue light emission)/electron transporting layer.
  • An electron blocking layer may be appropriately provided between each light emitting layer and a hole transporting layer or a space layer.
  • a hole blocking layer may be appropriately provided between each light emitting layer and an electron transporting layer.
  • An example of a typical device configuration of the tandem type organic EL device is the following device configuration.
  • first light emitting unit and the second light emitting unit can each be independently selected, for example, from the light emitting units as described above.
  • the intermediate layer is generally also referred to as intermediate electrode, intermediate conductive layer, charge generating layer, electron withdrawing layer, connection layer, or intermediate insulating layer, and a known material configuration in which electrons are supplied to the first light emitting unit and holes are supplied to the second light emitting unit can be used.
  • FIG. 1 is a schematic diagram illustrating an example of the configuration of the organic EL device of the present invention.
  • An organic EL device 1 includes a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 10 disposed between the anode 3 and the cathode 4 .
  • the light emitting unit 10 includes a light emitting layer 5 .
  • the organic EL device 1 includes a hole transporting zone 6 (hole injecting layer, hole transporting layer, etc.) between the light emitting layer 5 and the anode 3 , and an electron transporting zone 7 (electron injecting layer, electron transporting layer, etc.) between the light emitting layer 5 and the cathode 4 .
  • an electron blocking layer (not shown) may be provided on the anode 3 side of the light emitting layer 5 and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light emitting layer 5 .
  • This enables to trap electrons or holes in the light emitting layer 5 to further increase the efficiency of generating excitons in the light emitting layer 5 .
  • FIG. 2 is a schematic diagram illustrating another configuration of the organic EL device of the present invention.
  • An organic EL device 11 includes the substrate 2 , the anode 3 , the cathode 4 , and a light emitting unit 20 disposed between the anode 3 and the cathode 4 .
  • the light emitting unit 20 includes the light emitting layer 5 .
  • a hole transporting zone disposed between the anode 3 and the light emitting layer 5 is formed of a hole injecting layer 6 a , a first hole transporting layer 6 b , and a second hole transporting layer 6 c .
  • An electron transporting zone disposed between the light emitting layer 5 and the cathode 4 is formed of a first electron transporting layer 7 a and a second electron transporting layer 7 b.
  • FIG. 3 is a schematic diagram illustrating another configuration of the organic EL device of the present invention.
  • An organic EL device 12 includes the substrate 2 , the anode 3 , the cathode 4 , and a light emitting unit 30 disposed between the anode 3 and the cathode 4 .
  • the light emitting unit 30 includes the light emitting layer 5 .
  • a hole transporting zone disposed between the anode 3 and the light emitting layer 5 is formed of the hole injecting layer 6 a , the first hole transporting layer 6 b , the second hole transporting layer 6 c , and a third hole transporting layer 6 d .
  • An electron transporting zone disposed between the light emitting layer 5 and the cathode 4 is formed of the first electron transporting layer 7 a and the second electron transporting layer 7 b.
  • a host combined with a fluorescent dopant material is referred to as a fluorescent host
  • a host combined with a phosphorescent dopant material is referred to as a phosphorescent host.
  • the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure.
  • the phosphorescent host means a material that forms a phosphorescence emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescence emitting layer. The same applies to the fluorescent host.
  • the substrate is used as a support of the organic EL device.
  • a plate of glass, quartz, or a plastic can be used as the substrate.
  • a flexible substrate may be used as the substrate.
  • An example of the flexible substrate is a plastic substrate of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride.
  • An inorganic vapor deposition film can also be used.
  • a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like that has a high work function (specifically 4.0 eV or more) is preferably used.
  • a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like that has a high work function (specifically 4.0 eV or more) is preferably used.
  • Specific examples thereof include indium oxide-tin oxide (ITO: indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene.
  • nitride examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), cupper (Cu), palladium (Pd), titanium (Ti), and nitride of the metals (for example, titanium nitride).
  • a film of such a material is generally formed by a spattering method.
  • indium oxide-zinc oxide can be formed by a spattering method by using a target obtained by adding to indium oxide 1 to 10 wt % of zinc oxide based on the indium oxide
  • indium oxide containing tungsten oxide and zinc oxide can be formed by a spattering method by using a target obtained by adding to indium oxide 0.5 to 5 wt % of tungsten oxide and 0.1 to 1 wt % of zinc oxide based on the indium oxide.
  • a film of such a material may be produced by a vacuum vapor deposition method, a coating method, an inkjet method, a spin-coating method, or the like.
  • the organic layer may include a hole transporting zone between the anode and the light emitting layer.
  • the hole transporting zone is composed of a hole injecting layer, a hole transporting layer, an electron blocking layer, and the like.
  • the hole transporting zone contains the inventive compound. It is preferable that at least one layer of these layers constituting the hole transporting layer contains the inventive compound, and it is particularly preferable that the hole transporting layer contains the inventive compound.
  • the hole injecting layer formed in contact with the anode is, regardless of the work function of the anode, formed by using a material in which hole injection is easy, and thus a material that is generally used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, or a mixture thereof, or an element belonging to the group 1 or 2 in the periodic table) can be used.
  • a material that is generally used as an electrode material for example, a metal, an alloy, an electrically conductive compound, or a mixture thereof, or an element belonging to the group 1 or 2 in the periodic table
  • An element belonging to the group 1 or 2 in the periodic table which is a material having a small work function, specifically, an alkali metal, such as lithium (Li) or cesium (Cs), or an alkaline earth metal, such as magnesium (Mg), calcium (Ca), or strontium (Sr), and an alloy containing them (for example, MgAg, AlLi), a rare earth metal, such as europium (Eu) or ytterbium (Yb), or an alloy containing them, or the like, can be used.
  • an alkali metal such as lithium (Li) or cesium (Cs)
  • an alkaline earth metal such as magnesium (Mg), calcium (Ca), or strontium (Sr)
  • an alloy containing them for example, MgAg, AlLi
  • a rare earth metal such as europium (Eu) or ytterbium (Yb), or an alloy containing them, or the like
  • the hole injecting layer is a layer containing a material having a high hole injecting capability (hole injecting material), and is formed between the anode and the light emitting layer, or between a hole transporting layer, if present, and the anode.
  • hole injecting material a material having a high hole injecting capability
  • molybdenum oxide titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like can be used.
  • a material for the hole injecting layer include aromatic amine compounds, such as 4,4′,4′′-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4′′-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4′-bis(N- ⁇ 4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl ⁇ -N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(N-
  • a high-molecular weight compound (oligomer, dendrimer, polymer, or the like) can also be used.
  • the high-molecular weight compound include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4- ⁇ N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino ⁇ phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation: Poly-TPD).
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N′-[4-(4-diphenylamino
  • a high-molecular weight compound with an acid such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrenesulfonic acid) (PAni/PSS), added thereto can also be used.
  • an acid such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrenesulfonic acid) (PAni/PSS)
  • an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K), is also preferably used.
  • HAT hexaazatriphenylene
  • R 221 to R 226 each independently represent a cyano group, —CONH 2 , a carboxy group, or —COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms).
  • Adjacent two selected from R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 may be bonded to each other to form a group represented by —CO—O—CO—.
  • R 227 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the hole transporting layer is a layer containing a material having a high hole transporting capability (hole transporting material), and is formed between the anode and the light emitting layer or between a hole injecting layer, if present, and the light emitting layer.
  • the inventive compound may be used, for the hole transporting layer, alone or in combination with the following compound.
  • the hole transporting layer may have a monolayer structure or a multilayer structure including two or more layers.
  • the hole transporting layer may have a two-layer structure including a first hole transporting layer (anode side) and a second hole transporting layer (cathode side). That is, the hole transporting zone may include a first hole transporting layer on the anode side and a second hole transporting layer on the cathode side.
  • the hole transporting layer may have a three-layer structure including, in order from the anode side, a first hole transporting layer, a second hole transporting layer, and a third hole transporting layer. That is, the third hole transporting layer may be arranged between the second hole transporting layer and the light emitting layer.
  • the hole transporting layer of the monolayer structure is preferably adjacent to the light emitting layer, and the hole transporting layer that is the nearest to the cathode in the multilayer structure, for example, the second hole transporting layer in the two-layer structure and the third hole transporting layer in the three-layer structure are preferably adjacent to the light emitting layer.
  • an electron blocking layer as described later or the like may be interposed between the hole transporting layer of the monolayer structure and the light emitting layer or between the hole transporting layer that is the nearest to the light emitting layer in the multilayer structure and the light emitting layer.
  • the hole transporting layer has a two-layer structure
  • at least one of the first hole transporting layer and the second hole transporting layer contains the inventive compound. That is, the inventive compound is contained only in the first hole transporting layer, or only in the second hole transporting layer, or in both the first hole transporting layer and the second hole transporting layer.
  • the inventive compound is preferably contained in the second hole transporting layer. That is, it is preferable that the inventive compound is contained only in the second hole transporting layer, or the inventive compound is contained in the first hole transporting layer and the second hole transporting layer.
  • the hole transporting layer has a three-layer structure
  • at least one of the first to third hole transporting layers contains the inventive compound. That is, the inventive compound is contained only in one layer selected from the first to third hole transporting layers (only in the first hole transporting layer, only in the second hole transporting layer, or only in the third hole transporting layer), only in two layers selected from the first to third hole transporting layers (only in the first hole transporting layer and the second hole transporting layer, only in the first hole transporting layer and the third hole transporting layer, or only in the second hole transporting layer and the third hole transporting layer), or in all of the first to third hole transporting layers.
  • the inventive compound is preferably contained in the third hole transporting layer. That is, it is preferable that the inventive compound is contained only in the third hole transporting layer, or the inventive compound is contained in the third hole transporting layer and one or both of the first hole transporting layer and the second hole transporting layer.
  • the inventive compound contained in each of the hole transporting layers is preferably a light hydrogen form from the viewpoint of the production cost.
  • the light hydrogen form refers to the inventive compound in which all the hydrogen atoms are a light hydrogen atom.
  • the present invention includes an organic EL device in which one or both of the first hole transporting layer and the second hole transporting layer (in the case of a two-layer structure), or at least one of the first to third hole transporting layers contain the inventive compound essentially constituted only of light hydrogen forms.
  • inventive compound essentially constituted only of light hydrogen forms means that the content of the light hydrogen form based on the total amount of the inventive compound is 90% by mole or more, preferably 95% by mole or more, and more preferably 99% by mole or more (each including 100%).
  • an aromatic amine compound for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative can be used.
  • aromatic amine compound examples include 4,4′-bis[N-(1-naphtyl)-N-phenylamino]biphenyl (abbreviation: NPB) and N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4′′-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4′′-tris[N-(3-methylphenyl)-N-phenylamino]tri
  • carbazole derivative examples include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).
  • anthracene derivative examples include 2-t-butyl-9,10-di(2-naphtyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphtyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).
  • t-BuDNA 2-t-butyl-9,10-di(2-naphtyl)anthracene
  • DNA 9,10-di(2-naphtyl)anthracene
  • DPAnth 9,10-diphenylanthracene
  • a high-molecular weight compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA), can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • the first hole transporting layer preferably contains one or more compounds represented by the following formula (11) or formula (12).
  • first hole transporting layer and the second hole transporting layer contain one or more compounds represented by the following formula (11) or (12).
  • an organic EL device of the present invention having a hole transporting layer having an n-layer structure (n is an integer of 4 or more), it is preferable that at least one layer of the first hole transporting layer to the (n ⁇ 1)th hole transporting layer contains one or more compounds represented by the following formula (11) or formula (12).
  • A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
  • At least one of A1, B1 and C1 and in the formula (12), at least one of A2, B2, C2 and D2 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group.
  • the fluorenyl group that A1, B1, C1, A2, B2, C2, and D2 might be may have a substituent at site 9, for example, it may be a 9,9-dimethylfluorenyl group, or a 9,9-diphenylfluorenyl group. Further, the substituents at site 9 may form a ring with each other, for example, the substituents at site 9 may form a fluorene skeleton or a xanthene skeleton with each other.
  • L Aa , L B1 L C1 , L A2 , L B2 , L C2 and L D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • the light emitting layer is a layer containing a material having a high light emitting capability (dopant material), and various materials can be used.
  • a fluorescence emitting material or a phosphorescence emitting material can be used as the dopant material.
  • a fluorescence emitting material is a compound that emits light from the singlet excited state
  • a phosphorescence emitting material is a compound that emits light from the triplet excited state.
  • the light emitting layer is a single layer.
  • the light emitting layer includes a first light emitting layer and a second light emitting layer.
  • a blue fluorescence emitting material that can be used in the light emitting layer
  • a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, or the like can be used.
  • N,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine abbreviation: YGA2S
  • 4-(9H-carbazol-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine abbreviation: YGAPA
  • 4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine abbreviation: PCBAPA.
  • an aromatic amine derivative or the like can be used as a green fluorescence emitting material that can be used in the light emitting layer.
  • an aromatic amine derivative or the like include N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N′,N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,N′,N′-triphenyl-1,4-phenylenediamine (abb
  • a red fluorescence emitting material that can be used in the light emitting layer
  • a tetracene derivative, a diamine derivative, or the like can be used.
  • Specific examples thereof include N,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD) and 7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acetonaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).
  • the light emitting layer contains a fluorescence emitting material (fluorescent dopant material).
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex
  • Specific examples thereof include bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3′,5′-bistrifluoromethylphenyl)pyridinato-N,C2′]iridium(III) picolinate (abbreviation: Ir(CF
  • an iridium complex or the like is used as a green phosphorescence emitting material that can be used in the light emitting layer.
  • examples thereof include tris(2-phenylpyridinato-N,C2′)iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2′)iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex
  • organic metal complexes such as bis[2-(2′-benzo[4,5- ⁇ ]thienyl)pyridinato-N,C3′]iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2′)iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,
  • a rare earth metal complex such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), or tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)), emits light from rare earth metal ions (electron transition between different multiplicities) and thus, can be used as a phosphorescence emitting material.
  • Tb(acac)3(Phen) tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III)
  • the light emitting layer may have a configuration in which such a dopant material as described above is dispersed in another material (host material).
  • a material that has a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the dopant material is preferably used.
  • the host material for example,
  • a metal complex such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), or bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);
  • Alq tris(8-quinolinolato)aluminum
  • the following anthracene compounds are preferably used as a host material.
  • the organic EL device when the light emitting layer includes a first light emitting layer and a second light emitting layer, at least one of the components constituting the first light emitting layer is different from the components constituting the second light emitting layer.
  • the dopant material contained in the first light emitting layer is different from the dopant material contained in the second light emitting layer, or the host material contained in the first light emitting layer is different from the host material contained in the second light emitting layer.
  • the light emitting layer may contain a light emitting compound (hereinafter sometimes simply referred to as a “fluorescent compound”) that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less.
  • a light emitting compound hereinafter sometimes simply referred to as a “fluorescent compound” that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less.
  • a method for measuring the main peak wavelength of a compound is as follows.
  • a 5 ⁇ mol/L toluene solution of a compound to be measured is prepared and placed in a quartz cell, and the emission spectrum of the sample (vertical axis: emission intensity, horizontal axis: wavelength) is measured at room temperature (300K).
  • the emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd.
  • the emission spectrum measuring device is not limited to the device used herein.
  • a peak wavelength of an emission spectrum at which the emission intensity is maximum is defined as the main peak wavelength.
  • the main peak wavelength may be referred to as fluorescent light emission main peak wavelength (FL-peak).
  • the fluorescent compound may be the dopant material or the host material.
  • the light emitting layer is a single layer
  • only one of the dopant material and the host material may be the fluorescent compound, or both may be the fluorescent compound.
  • the light emitting layer includes a first light emitting layer (anode side) and a second light emitting layer (cathode side)
  • first light emitting layer and the second light emitting layer may contain the fluorescent compound, or both of the light emitting layers may contain the fluorescent compound.
  • first light emitting layer contains the fluorescent compound
  • second light emitting layer contains the fluorescent compound
  • only one of the dopant material and the host material contained in the second light emitting layer may be the fluorescent compound, or both may be the fluorescent compound.
  • the electron transporting layer is a layer containing a material having a high electron transporting capability (electron transporting material), and is formed between the light emitting layer and the cathode or between an electron injecting layer, if present, and the light emitting layer.
  • electron transporting material a material having a high electron transporting capability
  • the electron transporting layer may have a monolayer structure or a multilayer structure including two or more layers.
  • the electron transporting layer may have a two-layer structure including a first electron transporting layer (anode side) and a second electron transporting layer (cathode side).
  • the electron transporting layer in the monolayer structure is preferably adjacent to the light emitting layer, and the electron transporting layer that is the nearest to the anode in the multilayer configuration, for example, the first electron transporting layer of the two-layer structure, is preferably adjacent to the light emitting layer.
  • a hole blocking layer as described later or the like may be interposed between the electron transporting layer of the monolayer structure and the light emitting layer or between the electron transporting layer that is the nearest to the light emitting layer in the multilayer structure and the light emitting layer.
  • the electron transporting layer for example,
  • Examples of the metal complex include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).
  • heteroaromatic compound examples include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxa
  • high-molecular weight compound examples include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).
  • the materials are materials having an electron mobility of 10 ⁇ 6 cm 2 /Vs or more. Materials other than those as mentioned above may be used for the electron transporting layer so long as they are materials higher in the electron transporting capability rather than in the hole transporting capability.
  • the electron injecting layer is a layer containing a material having a high electron injecting capability.
  • an alkali metal such as lithium (Li) or cesium (Cs)
  • an alkaline earth metal such as magnesium (Mg), calcium (Ca), or strontium (Sr)
  • Mg magnesium
  • Ca calcium
  • a rare earth metal such as europium (Eu) or ytterbium (Yb)
  • a compound containing them can be used.
  • Examples of the compound include an alkali metal oxide, an alkali metal halide, an alkali metal-containing organic complex, an alkaline earth metal oxide, an alkaline earth metal halide, an alkaline earth metal-containing organic complex, a rare earth metal oxide, a rare earth metal halide, and a rare earth metal-containing organic complex.
  • two or more of the compounds can be used in mixture.
  • a material in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a material having electron transporting capability specifically, a material in which magnesium (Mg) is contained in Alq, or the like, may be used. In this case, electron injection from the cathode can be more efficiently achieved.
  • a composite material obtained by mixing an organic compound with an electron doner may be used in the electron injecting layer.
  • Such a composite material is excellent in the electron injecting capability and the electron transporting capability because the organic compound receives electrons from the electron doner.
  • the organic compound is preferably a material excellent in transporting received electrons, and specifically, a material constituting the aforementioned electron transporting layer (such as a metal complex or a heteroaromatic compound) can be used.
  • the electron donor a material having an electron donation capability for an organic compound can be used.
  • an alkali metal, an alkaline earth metal, and a rare earth metal are preferred, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • An alkali metal oxide or an alkaline earth metal oxide is also preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide.
  • a Lewis base such as magnesium oxide, can also be used.
  • a metal, an alloy, an electrically conductive compound, or a mixture thereof that has a low work function (specifically 3.8 eV or less) is preferably used for the cathode.
  • a cathode material include elements belonging to the group 1 or 2 of the periodic table, that is, an alkali metal, such as lithium (Li) or cesium (Cs), an alkaline earth metal, such as magnesium (Mg), calcium (Ca), or strontium (Sr), and an alloy containing them (for example, MgAg, AlLi), and a rare earth metal, such as europium (Eu) or ytterbium (Yb), and an alloy containing them.
  • an alkali metal such as lithium (Li) or cesium (Cs)
  • an alkaline earth metal such as magnesium (Mg), calcium (Ca), or strontium (Sr)
  • an alloy containing them for example, MgAg, AlLi
  • a rare earth metal such as europium (E
  • the cathode is formed by using an alkali metal, an alkaline earth metal, and an alloy containing them, a vacuum vapor deposition method or a sputtering method can be adopted.
  • a coating method, an inkjet method, or the like can be adopted.
  • the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function.
  • a film of such a conductive material can be formed by using a sputtering method, an inkjet method, a spin-coating method, or the like.
  • the organic EL device applies an electric field to an ultrathin film, and thus, pixel defects are likely to occur due to leaks or short-circuiting.
  • an insulating layer formed of an insulating thin film layer may be inserted between a pair of electrodes.
  • Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. A mixture or a laminate of them may also be used.
  • the space layer is, for example, a layer provided between a fluorescence emitting layer and a phosphorescence emitting layer for the purpose of preventing excitons generated in the phosphorescence emitting layer from diffusing into the fluorescence emitting layer, or adjusting the carrier balance, in the case where the fluorescence emitting layers and the phosphorescence emitting layers are stacked.
  • the space layer can also be provided between two or more phosphorescence emitting layers.
  • the space layer is provided between the light emitting layers, a material having both an electron transporting capability and a hole transporting capability is preferred.
  • one having a triplet energy of 2.6 eV or more is preferred in order to prevent diffusion of the triplet energy in the adjacent phosphorescence emitting layers.
  • Examples of the material used for the space layer include the same as those used for the hole transporting layer as described above.
  • a blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer, may be provided adjacent to the light emitting layer.
  • the electron blocking layer is a layer that prevents electrons from leaking from the light emitting layer to a hole transporting layer
  • the hole blocking layer is a layer that prevents holes from leaking from the light emitting layer to an electron transporting layer.
  • the exciton blocking layer functions to prevent excitons generated in the light emitting layer from diffusing into the surrounding layers to trap the excitons within the light emitting layer.
  • Each layer of the organic EL device can be formed by a conventionally known vapor deposition method, a coating method, or the like.
  • each layer can be formed by a known technique by a vapor deposition method, such as a vacuum vapor deposition method or a molecular beam vapor deposition method (MBE method), or a coating method using a solution of a compound for forming a layer, such as a dipping method, a spin-coating method, a casting method, a bar-coating method, and a roll-coating method.
  • a vapor deposition method such as a vacuum vapor deposition method or a molecular beam vapor deposition method (MBE method)
  • MBE method molecular beam vapor deposition method
  • a coating method using a solution of a compound for forming a layer such as a dipping method, a spin-coating method, a casting method, a bar-coating method, and a roll-coating method.
  • the film thickness of each layer is not particularly limited, but is typically 5 nm to 10 ⁇ m, and more preferably 10 nm to 0.2 ⁇ m because in general, when the film thickness is too small, defects such as pinholes are likely to occur, and conversely, when the film thickness is too large, a high driving voltage is required and the efficiency decreases.
  • a total thickness of the first hole transporting layer and the second hole transporting layer is preferably 30 nm or more and 150 nm or less, and more preferably 40 nm or more and 130 nm or less.
  • the thickness of the second hole transporting layer having a two-layer structure or a three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, and particularly preferably 35 nm or more, and is preferably 100 nm or less.
  • the thickness of the hole transporting layer adjacent to the light emitting layer is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, and particularly preferably 30 nm or more, and is preferably 100 nm or less.
  • the ratio of a film thickness D2 of the second hole transporting layer to a film thickness D1 of the first hole transporting layer is preferably 0.3 ⁇ D2/D1 ⁇ 4.0, more preferably 0.5 ⁇ D2/D1 ⁇ 3.5, and further preferably 0.75 ⁇ D2/D1 ⁇ 3.0.
  • the organic EL device can be used in an electronic instrument, such as a display apparatus and a light emitting apparatus.
  • the display apparatus include a display component of an organic EL panel module or the like, a television, a mobile phone, a tablet, and a personal computer.
  • the light emitting apparatus include a lighting or a vehicle lamp.
  • the organic EL device can be used in an electronic instrument, such as a display component of an organic EL panel module or the like, a display apparatus of a television, a mobile phone, a personal computer, or the like, and a light emitting apparatus of a lighting or a vehicle lamp.
  • an electronic instrument such as a display component of an organic EL panel module or the like, a display apparatus of a television, a mobile phone, a personal computer, or the like, and a light emitting apparatus of a lighting or a vehicle lamp.
  • a glass substrate of 25 mm ⁇ 75 mm ⁇ 1.1 mm with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes.
  • the film thickness of the ITO was 130 nm.
  • the cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and firstly, Compound HT-1 and Compound HA were vapor co-deposited on the surface having the transparent electrode formed thereon so as to cover the transparent electrode, thus forming a hole injecting layer with a film thickness of 10 nm.
  • the mass ratio of Compound HT-1 and Compound HA was 97:3.
  • Compound HT-1 was vapor deposited to form a first hole transporting layer with a film thickness of 40 nm.
  • Compound Inv-1 was vapor deposited to form a second hole transporting layer with a film thickness of 5 nm.
  • Compound BH-1 (host material) and Compound BD-1 (dopant material) were vapor co-deposited to form a first light emitting layer with a film thickness of 10 nm.
  • the mass ratio of Compound BH-1 and Compound BD-1 (BH-1:BD-1) was 99:1.
  • Compound BH-2 (host material) and Compound BD-1 (dopant material) were vapor co-deposited to form a second light emitting layer with a film thickness of 10 nm.
  • the mass ratio of Compound BH-2 and Compound BD-1 (BH-2:BD-1) was 99:1.
  • Compound ET-1 was vapor deposited to form a first electron transporting layer with a film thickness of 5 nm.
  • Compound ET-2 and Liq were vapor co-deposited to form a second electron transporting layer with a film thickness of 25 nm.
  • the mass ratio of Compound ET-2 and Liq was 50:50.
  • Yb was vapor deposited to form an electron injecting electrode with a film thickness of 1 nm.
  • metal A1 was vapor deposited to form a metal cathode with a film thickness of 50 nm.
  • the layer configuration of the organic EL device (I) of Example 1 thus obtained was as follows.
  • the numerals in parentheses each indicate the film thickness (nm), and the ratios are each a mass ratio.
  • Each organic EL device (I) was produced in the same manner as in Example 1 except for using a comparative compound Ref-1 instead of the inventive compound Inv-1.
  • the resulting organic EL device (I) was driven with a constant direct current at a current density of 50 mA/cm 2 , and the period of time until the luminance was reduced to 95% of the initial luminance was measured, and was defined as 95% lifetime (LT95).
  • the Compound Inv-1 provides an organic EL device with a longer lifetime than that of the Comparative Compound Ref-1.
  • a glass substrate of 25 mm ⁇ 75 mm ⁇ 1.1 mm with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes.
  • the film thickness of the ITO was 130 nm.
  • the cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and firstly, Compound HT-2 and Compound HA were vapor co-deposited on the surface having the transparent electrode formed thereon so as to cover the transparent electrode, thus forming a hole injecting layer with a film thickness of 10 nm.
  • the mass ratio of Compound HT-2 and Compound HA (HT-2:HA) was 97:3.
  • Compound HT-2 was vapor deposited to form a first hole transporting layer with a film thickness of 85 nm.
  • Compound Inv-4 was vapor deposited to form a second hole transporting layer with a film thickness of 5 nm.
  • Compound BH-3 (host material) and Compound BD-2 (dopant material) were vapor co-deposited to form a first light emitting layer with a film thickness of 20 nm.
  • the mass ratio of Compound BH-3 and Compound BD-2 (BH-3:BD-2) was 99:1.
  • Compound ET-3 was vapor deposited to form a first electron transporting layer with a film thickness of 5 nm.
  • Compound ET-4 and Liq were vapor co-deposited to form a second electron transporting layer with a film thickness of 31 nm.
  • the mass ratio of Compound ET-4 and Liq (ET-4:Liq) was 50:50.
  • Liq was vapor deposited to form an electron injecting electrode with a film thickness of 1 nm.
  • metal A1 was vapor deposited to form a metal cathode with a film thickness of 80 nm.
  • the layer configuration of the organic EL device (II) of Example 2 thus obtained was as follows.
  • the numerals in parentheses each indicate the film thickness (nm), and the ratios are each a mass ratio.
  • An organic EL device (II) was produced in the same manner as in Example 2 except for using the compounds shown in Table 2 instead of the Compound Inv-2.
  • the 95% lifetime (LT95) of the resulting organic EL device (II) was measured in the same manner as the evaluation of the organic EL device (I). The results are shown in Table 2.
  • the Compounds Inv-4 to 12 and 20 provide an organic EL device with a longer lifetime than that of the Comparative Compound Ref-2.
  • a glass substrate of 25 mm ⁇ 75 mm ⁇ 1.1 mm with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes.
  • the film thickness of the ITO was 130 nm.
  • the cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and firstly, Compound HT-3 and Compound HA were vapor co-deposited on the surface having the transparent electrode formed thereon so as to cover the transparent electrode, thus forming a hole injecting layer with a film thickness of 10 nm.
  • the mass ratio of Compound HT-3 and Compound HA (HT-3:HA) was 97:3.
  • Compound HT-3 was vapor deposited to form a first hole transporting layer with a film thickness of 80 nm.
  • Compound Inv-13 was vapor deposited to form a second hole transporting layer with a film thickness of 7.5 nm.
  • BH host material
  • BD-3 dopant material
  • This BH:BD-3 film functions as a light emitting layer.
  • the BH [Compounds BH-4 and BH-5 (both host materials)] contained in the light emitting layer have a mass ratio of 3:2, and the concentration of BD-3 is 2% by mass with respect to the entire light emitting layer.
  • Compound ET-5 was vapor deposited to form a first electron transporting layer with a film thickness of 5 nm.
  • Compound ET-6 and Liq were vapor co-deposited to form a second electron transporting layer with a film thickness of 25 nm.
  • the mass ratio of Compound ET-6 and Liq (ET-6:Liq) was 67:33.
  • Yb was vapor deposited to form an electron injecting electrode with a film thickness of 1 nm.
  • metal A1 was vapor deposited to form a metal cathode with a film thickness of 80 nm.
  • the layer configuration of the organic EL device (III) of Example 12 thus obtained was as follows.
  • the numerals in parentheses each indicate the film thickness (nm), and the ratios are each a mass ratio.
  • An organic EL device (III) was produced in the same manner as in Example 12 except for using the compounds shown in Table 3 instead of the Compound Inv-13.
  • the Compounds Inv-13 to 19 provide an organic EL device with a longer lifetime than that of the Comparative Compound Ref-3.

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  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
US18/558,390 2022-04-12 2023-04-06 Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device Pending US20240324450A1 (en)

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